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Synthesis of Homoprotoberberines and 8-Oxoprotoberberines by Sequential Bicyclization of Phenylacetamides
Tetrahedron ( IF 2.1 ) Pub Date : 11 February 2000 , DOI: 10.1016/s0040-4020(99)01084-4
Rafael Suau , Juan Manuel López-Romero , Antonio Ruiz , Rodrigo Rico

The reaction of phenylacetamides with oxalyl chloride/Lewis acid provides a convergent, high-yield entry to C-homoprotoberberine and 8-oxoprotoberberine alkaloids from available starting materials. This approach was used to synthesize 8-oxopseudopalmatine starting from N-[β-(3′,4′-dimethoxyphenyl)ethyl]-3,4-dimethoxyphenylacetamide. Some C-homoprotoberberines exhibit significant cytotoxicity against human breast carcinoma cells.

中文翻译:

苯乙酰胺的顺序双环化合成高原小ber碱和8-氧原小ber碱

苯乙酰胺与草酰氯/路易斯酸的反应提供了从可用起始原料到C-高伯小ber碱和8-氧伯小o碱生物碱的收敛,高收率的入口。该方法用于从N- [β-(3',4'-二甲氧基苯基)乙基] -3,4-二甲氧基苯基乙酰胺开始合成8-氧代伪巴马汀。一些C-同型小ber碱对人乳腺癌细胞显示出显着的细胞毒性。
更新日期:2017-01-31
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